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Metal-free-mediated synthesis of fulleropyrrolines by the reaction of [60]fullerene with β-substituted ethylamines

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Abstract

The reaction of [60]fullerene with β-substituted ethylamines under air conditions afforded unexpected fulleropyrrolines with trisubstituted alkene functional groups in moderate yields. The conversion of β-substituted ethylamines to their corresponding aldehydes played a crucial role in the successful synthesis of fulleropyrrolines. Promoted by p-toluenesulfonic acid, the obtained fulleropyrroline could (1) be converted back to [60]fullerene in nearly quantitative yield and (2) further react with 1,3-propanediol to generate fullerene-fused dioxepane.

Graphical abstract: Metal-free-mediated synthesis of fulleropyrrolines by the reaction of [60]fullerene with β-substituted ethylamines

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Publication details

The article was received on 03 Apr 2017, accepted on 25 Jul 2017 and first published on 25 Jul 2017


Article type: Letter
DOI: 10.1039/C7NJ01101F
Citation: New J. Chem., 2017, Advance Article
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    Metal-free-mediated synthesis of fulleropyrrolines by the reaction of [60]fullerene with β-substituted ethylamines

    J. Xiang, C. Huang, H. Wang, F. Li, J. Shi, Y. Huang, L. Liu, C. Liu, A. M. Asiri and K. A. Alamry, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ01101F

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